Photoelectrochemical Asymmetric Catalysis Enables Enantioselective Heteroarylcyanation of Alkenes via C–H Functionalization,Journal of the American Chemical Society

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Photoelectrochemical Asymmetric Catalysis Enables Enantioselective Heteroarylcyanation of Alkenes via C–H Functionalization
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2023-08-15 , DOI: 10.1021/jacs.3c07146
Xiao-Li Lai ₁ , Hai-Chao Xu ₁

Affiliation

The asymmetric difunctionalization of alkenes, a method transforming readily accessible alkenes into enantioenriched chiral structures of high value, has long been a focal point of organic synthesis. Despite tremendous efforts in this domain, it remains a considerable challenge to devise enantioselective oxidative dicarbofunctionalization of alkenes, even though these transformations can utilize stable and unfunctionalized functional group donors. In this context, we report herein a photoelectrocatalytic method for the enantioselective heteroarylcyanation of aryl alkenes, which employs unfunctionalized heteroarenes through C–H functionalization. The photoelectrochemical asymmetric catalysis (PEAC) method combines photoredox catalysis and asymmetric electrocatalysis to facilitate the formation of two C–C bonds operating via hydrogen (H₂) evolution and obviating the need for external chemical oxidants.

中文翻译：

光电化学不对称催化通过C-H官能化实现烯烃的对映选择性杂芳氰化

烯烃的不对称双官能化是一种将容易获得的烯烃转化为高价值的对映体富集的手性结构的方法，长期以来一直是有机合成的焦点。尽管在这一领域做出了巨大的努力，但设计烯烃的对映选择性氧化二碳官能化仍然是一个相当大的挑战，即使这些转化可以利用稳定和非官能化的官能团供体。在此背景下，我们在此报告了一种用于芳基烯烃对映选择性杂芳基氰化的光电催化方法，该方法通过 C-H 官能化使用未官能化的杂芳烃。_{光电化学不对称催化（PEAC）方法结合了光氧化还原催化和不对称电催化，以促进通过析氢（H 2}）释放操作的两个C-C键的形成，并且无需外部化学氧化剂。

更新日期：2023-08-15

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